The nitrogen-rich energetic compound 4-carboxamide-5-(1: H -tetrazol-5-yl)-1 H -1,2,3-triazole and its 1D sodium complex: Synthesis and properties

Article abstract of DOI:10.1039/c6ra22151c

The new nitrogen-rich energetic compound 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole (2) and its sodium complex (3) have been synthesized using diaminomaleodinitrile as the starting material in a three step synthesis. Both of the compounds were comprehensively characterized using Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS) and elemental analysis (EA). The sodium complex of 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole was confirmed using single-crystal X-ray diffraction for the first time. The thermal stability of the two compounds has been measured using differential scanning calorimetry (DSC), which indicated that the decomposition peak temperatures were 332.6 °C (2) and 374.1 °C (3). The density and enthalpy of formation of 2 were calculated with Gaussian 09 and the detonation pressure (21.9 GPa) and the detonation velocity (7182 m s^-1) were predicted by Kamlet-Jacobs equations. Compound 2 was not sensitive to impact (>40 J) or friction (>360 N).

Full text of DOI:10.1039/c6ra22151c

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Page 1 of 18
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Nitrogen-rich energetic compounds of
4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole and its
1D sodium complex: synthesis and properties
Jian Qin, Tong Li, Jian-Guo Zhang*, Zhi-Bin Zhang
∗ Prof. Dr. J.ꢀG. Zhang
Fax: +86ꢀ10ꢀ68918091
EꢀMail: zjgbit@bit.edu.cn
State Key Laboratory of Explosion Science and Technology,
Beijing Institute of Technology, Beijing 100081, P. R. China
1

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Abstract
The
new
nitrogenꢀrich
energetic
compound
of
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (2) and its sodium complex (3) had
been synthesized by using diaminomaleodinitrile as the starting material in a three step synꢀ
thesis. Both of them were comprehensively characterized by using the Fourier transꢀ
formꢀinfrared spectroscopy (FTꢀIR), Mass spectrometry (MS) and elemental analysis (EA).
Sodium complex of 4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole confirmed by sinꢀ
gleꢀcrystal Xꢀray diffraction for the first time. The thermal stability of two compounds had
been measured by differential scanning calorimetry (DSC), which indicated that the decomꢀ
position peak temperature were 332.6 °C (2) and 374.1 °C (3) respectively. The density and
enthalpy of formation of 2 were calculated with Gaussian 09 and detonation pressure (21.9
GPa) and detonation velocity (7182 m sꢀ1) were predicted by KamletꢀJacobs equations.
Compound 2 was insensitive towards impact (>40J) and friction (>360N).
Keywords: Synthesis; 1,2,3ꢀtriazoles; nitrogenꢀrich compounds
1. Introduction
Nitrogenꢀrich compounds have been worldꢀwide working in the field of energetic
materials in the recent years. The high nitrogen content of compounds results high
potential as explosive due to the large number of inherent N–N, N=N and C–N
bonds.1ꢀ3 Recently, lots of studies of new high energy density materials (HEDM) conꢀ
tinues to focus on the derivatives of furazan4ꢀ6, triazole7ꢀ10 and tetrazole11ꢀ14. Furꢀ
thermore, the nitrogenꢀrich compounds are green and environmental protection which
mainly release nontoxic N2 upon decompositions.15 In general, tetrazole is more enꢀ
ergetic but also more sensitive towards external stimuli, whereas triazoles
(1,2,3ꢀtriazole and 1,2,4ꢀtriazole) are less sensitive.16 In regard to the requirements of
detonation performance and safety, the triazole are the most promising backbones.
2

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At present, great number of studies concentrated on 1,2,4ꢀtriazoles17ꢀ22 and
salts23ꢀ25, but only few reports for derivatives of 1,2,3ꢀtriazoles and derivatives are
known. In 1992, it is first report on 4ꢀaminoꢀ5ꢀnitroꢀ1,2,3ꢀ2Hꢀtriazole (ANTZ)26 with
nitrogen content being 54%. ANTZ is a high energy candidate and also an important
intermediates of energy material. Surprisingly, ANTZ (Td, 297 °C) is more thermally
stable than 3ꢀaminoꢀ5ꢀnitroꢀ1,2,4ꢀtriazole (Td, 243 °C). The singleꢀcrystal structure of
4ꢀnitraminoꢀ5ꢀnitroꢀ1,2,3ꢀ2Hꢀtriazole27 with high density (1.919 g cmꢀ3)is obtained in
2003. So, the nitrogenꢀrich derivatives of 1,2,3ꢀtriazole is a very promising research
direction. Here, the goal of this study has therefore been the synthesis of nitroꢀ
genꢀrich
4,5ꢀsubstituted
1,2,3ꢀtriazole
(1, nitrogen
compounds:
content: 51%),
4ꢀcarboxamideꢀ5ꢀcyanoꢀ2Hꢀ1,2,3ꢀtriazole
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (2, nitrogen content: 62%), and
its Sodium complex (3). All of compounds are comprehensive characterized and the
decomposition temperature and kinetics parameters of 2 and 3 are obtained.
Results and discussion
Synthesis
There was a possible route to synthesize the new nitrogenꢀrich compound
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (2). The synthesis route was
described in Scheme 1. 4,5ꢀDicyanoꢀ2Hꢀ1,2,3ꢀtriazole28 was prepared by one step
reactions from diaminomaleodinitrile according to literature method.
4,5ꢀDicyanoꢀ2Hꢀtriazole could be hydrolysed with 1M HCl and 1M acetic acid to
obtain 4ꢀcarboxamideꢀ5ꢀcyanoꢀ2Hꢀ1,2,3ꢀtriazole (1) in 67% yield. The compound 1
could be recrystallized with hot water. The reaction of compound 1 with sodium azꢀ
ide
and
zinc
chloride
in
a
1,3ꢀdipolar
cycloaddition
achieved
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (2) in 78% yield. The sodium
complex of 4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (3) was syntheꢀ
sized by metathesis reaction of compound 2 and sodium hydroxide. The complex 3
was stable and could be stored for extended periods in air.
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Scheme 1. synthesis route toward 4ꢀcarboxamideꢀ5ꢀcyanoꢀ2Hꢀ1,2,3ꢀtriazole (1),
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (3).
(2),
Sodium
complex
of
Single-crystal X-ray structure analysis
The Xꢀray crystallographic data of compounds 1 hydrate and 3 were obtained with
A Rigaku AFCꢀ10/Saturn 724+ CCD diffractometer with graphite monoꢀchromated
MoꢀKα radiation. The structures were solved by direct methods using SHELXS9729
and refined anisotropically on F2 by the fullꢀmatrix leastꢀsquares technique using the
SHELXL9730 programs. Crystallographic data and structure refinements are summaꢀ
rized in Table 1 and can be obtained free of charge on quoting the depository numꢀ
bers CCDCꢀ1497228 (1) and CCDCꢀ1497227 (3),
Table 1. Crystallographic data and structure refinements for 1 H2O and 3
1 H2O
3
Empirical formula
MW (g molꢀ1)
Temperature (K)
Crystal System
Space Group
a (Å)
C4H5N5O2
155.13
C8H14N16Na2O6
476.33
298(2)
298(2)
Monoclinic
P2(1)/c
3.6672(3)
16.3613(14)
11.3345(8)
90.00
Triclinic
Pꢀ1
6.7660(6)
7.2849(7)
10.7541(9)
109.069(2)
98.9320(10)
103.404(2)
471.70(7)
1
b (Å)
c (Å)
α (°)
β (°)
97.7600(10)
90.00
γ (°)
V (Å)3
673.84(9)
4
Z
ρcalcd (g cmꢀ3)
ꢀ (mmꢀ1)
1.529
1.677
0.126
0.178
F (000)
320
244
Crystal size (mm)
θ (°)
0.40 x 0.10 x 0.07
3.08ꢀ25.01
3230
0.21 x 0.14 x 0.06
3.01ꢀ25.02
1631
Reflections collected
Unique reflections
1183
1631
4

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Rint
0.0809
0.0000
Data/restraints/parameters 1183 / 0 / 100
1631 / 0 / 147
1.042
GOF on F2
1.018
R1, wR2 [I>2σ(I)]
R1, wR2 (all data)
CCDC
R1=0.0556, wR2=0.1325 R1=0.0676, wR2=0.1680
R1=0.0894, wR2=0.1491 R1=0.0901, wR2=0.1811
1497228
1497227
The 4ꢀcarboxamideꢀ5ꢀcyanoꢀ2Hꢀ1,2,3ꢀtriazole hydrate (1) crystallized in the monꢀ
oclinic space group P21/c with four formula units per unit cell and a calculated denꢀ
sity of 1.529 g cm−3 at 298 K. As shown in Figure 1, The bond lengths in the
4,5ꢀsubstituted 1,2,3ꢀtriazole are between the length of the corresponding single and
double bonds. N1–N2 bond (1.320(3) Å) is almost the same as N2–N3 bond (1.323(3)
Å), and then triazole ring is symmetrical. Amide C1ꢀN4 bond (1.318(4) Å) is shorter
than single bonds, because amide group is almost planar and effect of unshared pair
electron of the nitrogen atom. C4–N5 bond of cyano (1.139(4) Å) is corresponding
triple bond. The intermolecular hydrogen bond is formed N5–H4⋯O1 between the
amide group and oxygen atom of neighboring amide (D⋯A: 2.173 Å; D–H⋯A:
167°). Between the amide group and a nitrogen atom of a neighboring triazole ring
which is also formed hydrogen bond N4–H4⋯N1 (D⋯A: 2.396 Å; D–H⋯A: 162°).
Moreover, the 4ꢀcarboxamideꢀ5ꢀcyanoꢀ2Hꢀ1,2,3ꢀtriazole crystallizes with one moleꢀ
cule water to form its monohydrate. Molecule features intermolecular hydrogen bond
N2–H2⋯O2 (D⋯A: 2.661 Å; D–H⋯A: 169°), O2–H2⋯O1 (D⋯A: 1.962 Å; D–
H⋯A: 156°), and O2–H2⋯N5 (D⋯A: 2.125 Å; D–H⋯A: 156°). Furthermore, the
detail information of the crystal structure determination has been compiled is in the
Supplementary information (Table S1&S2).
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（a）
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(b)
Figure 1. Molecular structure of 1 H2O (a), Hydrogen bonds and Unit cell packing of 1 H2O (b).
The
title
nitrogenꢀrich
sodium
complex
of
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (3) crystallized in the Triclinic
space group Pꢀ1 with one formula units per unit cell. The molecular unit is depicted
in Figure 2. The bond lengths of triazole and tetrazole are also between formal single
and double bonds. Furthermore, the bond lengths of triazole ring is different from
that of 1 H2O with N2–N3 and N3–N4 bond lengths of 1.310(5) and 1.341(4) Å reꢀ
spectively. It has been found that sodium form a chelated structure with the triazole
ring. The sodium ion displays an octahedral hexaꢀcoordinate complex which is coorꢀ
dinated by the nitrogen atoms N2, N3 of two triazole rings, oxygen atom O1 of amide
group and oxygen atom O2, O2, O3 of the coordinated water molecules. The comꢀ
plex 3 forms a 1D chainꢀlike structure constructed by coordination bonds. The strucꢀ
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ture is dominated by an extensive hydrogen bonding network involving three nitroꢀ
gen atoms and four oxygen atoms of the coordinated water molecules. The intermoꢀ
lecular hydrogen bond is formed N1–H1⋯N8 (D⋯A: 2.027 Å; D–H⋯A: 176°) and
N1–H1⋯N5 (D⋯A: 1.964 Å; D–H⋯A: 164°) between the amide group and nitrogen
atom of neighboring tetrazole (D⋯A: 2.173 Å; D–H⋯A: 167°). Between the nitrogen
atom of triazole ring and oxygen atoms of neighboring amide group which is also
formed hydrogen bond N4–H4⋯O1 (D⋯A: 2.013 Å; D–H⋯A: 160°). Moreover, inꢀ
termolecular hydrogen bonds between the coordinated water molecules and nitrogen
atom of tetrazole are O2–H2⋯N6 (D⋯A: 2.085 Å; D–H⋯A: 166°) and O3–H3⋯N7
(D⋯A: 2.061 Å; D–H⋯A: 158°). At last, there is the detail information of the crystal
structure determination h in the Supplementary information (Table S3&S4).
(a)
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(b)
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(c)
Figure 2. Molecular structure of 3 (a), 1D chainꢀlike structure of 3 (b),Hydrogen bonds and Unit
cell packing of 3 (c).
Thermal analyses
The differential scanning calorimetry (DSC) shows the thermal behaviors of 2 and
3 in the temperature range of 20ꢀ500 °C at the heating rate of 5 °C minꢀ1 (see Figure
3). Phase transition processes of 2 start at 200 °C with the peak temperature of
223.3 °C, which ends at 241 °C. It is a sharp exothermic process with the peak temꢀ
perature at 332.6 °C. For 3, it is found in the DSC curve that two exothermic stages
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appear. Two sharp exothermic process with the peak temperature appear at 374.1 °C
and 410.4 °C respectively. Both of them have the advantages of good thermal stabilꢀ
ity. Furthermore, 3 performs higher thermal stability than 2 in the high temperature
conditions.
Figure 3. DSC curves with a heating rate of 5°C minꢀ1
Non-Isothermal kinetics analysis
Kissinger’s method31 and OzawaꢀDoyle’s method32 are employed to determine the
apparent activation energy (E) and the preꢀexponential factor (A). The Kissinger (1)
and OzawaꢀDoyle (2) equations are as follows (Tp is peak temperature, °C; R is the
gas constant, 8.314 J molꢀ1 °C ꢀ1; β is the linear heating rate, °C minꢀ1 and C is a conꢀ
stant):
ꢁ
ꢈꢉꢊ
ꢋꢉ
ꢋꢉ
ln ꢀ ꢅ ꢆ ln ꢇ
ꢌ ꢍ
(1)
(2)
ꢂꢄ
ꢊꢂꢉ
ꢃ
0.4567ꢋꢏ
log ꢁ ꢎ
ꢆ ꢐ
ꢊꢂ
ꢃ
Based on the exothermic peak temperatures measured at four different heating
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rates of 5, 10, 15 and 20 °C minꢀ1, the kinetic parameters of 2 and 3 are calculated.
The apparent activation energy Ek and Eo, preꢀexponential factor A and linear correlaꢀ
tion coefficients Rk and Ro are shown in Table 2.
The calculated results using both methods are quite close, which are all in the
normal range of kinetic parameters for the thermal decomposition reaction of solid
materials.33 Using the obtained Ea (the average of Ek and Eo) and lnAk value, the Arꢀ
rhenius equations of 2 and 3 can be expressed as lnk = 20.29ꢀ257.9×103/RT (
= 20.19ꢀ275.1×103/RT (
) for the exothermic processes, which can be used to estiꢀ
2) and lnk
2
mate the rate constants of the initial thermal decomposition processes .
Table 2. Peak temperatures and kinetics parameters for 2 and 3
2
3
β
(°C minꢀ1)
Peak temperatures Tp (°C)
5
332.6
336.8
342.4
348.1
374.1
380.6
385.3
391.5
10
15
20
Kissinger’s method
Ek (kJ mol−1)
ln[Ak (s1−)]
259.4
20.29
276.7
20.19
Rk
ꢀ0.9636
ꢀ0.9831
Ozawa’s method
E
o (kJ mol−1)
256.4
273.5
R
o
ꢀ0.9662
ꢀ0.9844
Theoretical calculations and properties
The density and enthalpy of formation are two important parameters in energetic
materials. In this work, the enthalpy of formation was computed using the method of
atomization energy and density also was computed by the Gaussian 09 suite of proꢀ
grams. The geometric optimization of the structure and frequency analyze carried out
using B3LYP functional with the 6ꢀ311++G** basis set. The optimized structure was
characterized to be true local energy minima on the potential energy surface without
imaginary frequencies.
The detonation pressure and detonation velocity of energetic compound can be
calculated by using empirical KamletꢀJacobs equations34 with the value of enthalpy
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of formation and density. Where each term in equations 3 and 4 is defined as follows:
D, detonation velocity (m sꢀ1); P, detonation pressure (GPa); N, moles of detonation
ꢀ1
ꢒ
gases per gram explosive (mol g ); ꢑ, average molecular weight of these gases (g
molꢀ1); Q, heat of detonation (cal gꢀ1); and ρ, the loaded density of explosives (g
cmꢀ3).Table 3 listed all the calculated results. The title compound 2 had a high nitroꢀ
gen content (62.2%) and the calculated density, calculated detonation pressure and
detonation velocity were 1.67 g cm−3, 21.9 GPa and 7182 m sꢀ1 respectively.
ꢖ/ꢄꢙ
ꢘ 1 ꢎ 1.30ꢚ
ꢛ
ꢒꢖ/ꢄ
ꢓ ꢆ 1.01ꢔꢕꢑ ꢗꢖ/ꢄ
(3)
(4)
ꢒꢖ/ꢄ
ꢄ
ꢜ ꢆ 1.558ꢚ ꢕꢑ ꢗꢖ/ꢄ
For a further analysis, the HOMOꢀLUMO orbital was calculated to reveal the poꢀ
tential sensitivity of compound 2. As show in Figure 4, red part relates to the positive
area and green part relates to the negative area. In the HOMO orbital, electron disꢀ
tributes uniformly in the whole molecular, but in the LUMO orbital, it concentrates
on the triazole part and the amide group part without the tetrazole part. The energy
level difference between the HOMOꢀLUMO orbital is 5.99 eV, which can indicate
the sensitivity of the energetic material. Therefore, compound 2 can be considered as
a kind of highꢀenergy material with low sensitivity.
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Figure 4. HOMOꢀLUMO orbital
For initial safety testing, the impact and friction sensitivities of 2 were measured
by following BAM standard methods. The results also showed in Table 3. It is not
surprising that compound 2 is insensitive towards impact (>40J) and friction
(>360N).
Table 3. Energetic properties and detonation parameters of 2 compared with TNT and RDX
TNT35
C7H5O6N3
227.13
18.5
RDX36
C3H6N6O6
222.12
37.8
7.5
2
Formula
FW/g mol−1
Na/%
C4H4O1N8
180.05
62.2
ISb/J
>40
15
FSc/N
>360
223.3
332.6
ꢀ44.4
ꢀ79.9
1.67
>353
80.1
120
Tm d/°C
204.1
230.0
0
e
Td /°C
295.0
ꢀ24.7
ꢀ74
ꢁCO f/%
ꢁCO g/%
ꢀ21.6
1.82
2
ρh/g cm−3
ꢂfH° i/kJ mol−1
Pj/GPa
1.654
ꢀ67
537.77
21.9
80
21.3
34.9
8748
Dk/m s−1
7182
6881
[a] Nitrogen content. [b] Impact sensitivity. [c] Friction sensitivity. [d] Melting point. [e] Deꢀ
composition temperature. [f] Oxygen balance assuming the formation of CO respectively. [g]
CO2. [h] Calculated density. [i] Calculated enthalpy of formation. [j] Calculated detonation presꢀ
sure. [k] Calculated detonation velocity.
Experimental section
Material and instruments
All chemical reagents and solvents of analytical grade were obtained from comꢀ
mercial sources. Elemental analyses were performed on a Flash EA 1112 fully autoꢀ
matic trace element analyzer. The FTꢀIR spectra were recorder as KBr pellets on a
Bruker Equinox 55. Mass spectra were recorded on an Agilent 500ꢀMS.Differential
scanning calorimetry (DSC) was carried out on a model Pyrisꢀ1 differential scanning
calorimeter in static air. The singleꢀcrystal Xꢀray diffraction analysis was carried out
by on Bruker CCD areaꢀdetector diffractometer.
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4,5-Dicyano-2H-1,2,3-triazole
4,5ꢀDicyanoꢀ2Hꢀ1,2,3ꢀtriazole has been synthesized according to the reference
method.28
4-carboxamide-5-cyano-2H-1,2,3-triazole (1)
4,5ꢀDicyanoꢀ2Hꢀ1,2,3ꢀtriazole (2.38 g, 20 mmol) was refluxed in an aqueous soluꢀ
tion of AcOH (1 M 25mL) and HCl (1 M 25mL) for 30 min. The solution was cooled
°
to 0 C, whereby the precipitate formed was filtered off and recrystallized from hot
water to afford 1 hydrate colourless needles (1.84 g, 67%). IR (KBr, cm−1): 3545,
3481, 3397, 3305, 3242, 2918, 2850, 2606, 2263, 2151, 1942, 1705, 1612, 1521,
1434, 1366, 1215, 1145, 990, 953, 795, 720, 640. MS (ESIꢀ): m/z = 136.10 ([M]ꢀ).
EA for C4H3N5O1 (%): calcd: C 35.04, H 2.21; N 51.08; found: C 35.12, H 2.16, N
51.15.
4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole (2)
Compound 1 (1.37g 10 mmol) was dissolved in water (50 mL) and sodium azide
(0.78 g, 12 mmol) and zinc chloride (1.5 g, 11 mmol) were added. The reaction mixꢀ
ture was stirred and heated under reflux for 4 h. The solution was then cooled to amꢀ
bient temperature and concentrated hydrochloric acid (10 mL) was added while
°
cooling to 0 C. The precipitate was removed by filtration under suction and the
product was washed with cold water and ethanol to obtain the compound 2 (1.4g
78%). IR (KBr, cm−1): 3348, 3223, 3092, 2921, 2858, 27801, 1685, 1587, 1469, 1309,
1217, 1175, 1125, 1048, 992, 858, 714, 666. MS (ESIꢀ): m/z = 179.10 ([M]ꢀ). EA for
C4H4N8O1 (%): calcd: C 26.67, H 2.24; N 62.21; found: C 26.73, H 2.28, N 62.17.
Sodium complex of 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole (3)
Sodium hydroxide (0.08 g, 2 mmol) was added to a suspension of (2) (0.36 g, 2
mmol) and water (10 mL), the mixture was stirred at 50 °C for 1 h, the clear solution
was slowly evaporated and single crystals of 3 was obtained. IR (KBr, cm−1): 3569,
3408, 3181, 3052, 2917, 2849, 2693, 1696, 1632, 1580, 1510, 1416, 1310, 1267,
15

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1171, 1124, 1054, 1029, 999, 898, 795, 728, 654. MS (ESIꢀ): m/z = 179.10 ([M]ꢀ).
EA for C4H3N8O1 (%): calcd: C 23.77, H 1.50; N55.44; found: C 23.85, H 1.57, N
55.42.
Conclusion
In this work, the synthetic routes, structures and properties of
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole (2) and its sodium complex (3)
were report. Singleꢀcrystal structures of 3 was obtained for the first time and it
showed a 1D chainꢀlike structure that sodium ions form a chelated structure with the
triazole. Compound 2 (332.6 °C) and complex 3 (374.1 °C) had the advantage of
good thermal stability. The kinetic parameters of exothermal process of 2 and 3 were
calculated with Kissinger's and OzawaꢀDoyel's methods. The Arrhenius equation of 2
and 3 were obtained. The compound 2 had the high nitrogen contents (62%) and the
detonation pressure (21.9 GPa) and detonation velocity (7182 m sꢀ1) were calculated
by using KamletꢀJacobs equations. The impact sensitive (>40J) and friction sensitive
(>360N) of 2 were measured. Based on detonation properties and stabilities,
4ꢀcarboxamideꢀ5ꢀ(1Hꢀtetrazolꢀ5ꢀyl)ꢀ1Hꢀ1,2,3ꢀtriazole was an insensitive energetic
material.
Acknowledgements
We gratefully acknowledge the support of the National Natural Science Foundaꢀ
tion of China (10776002), and the project of State Key Laboratory of Science and
Technology (No. YBT16ꢀ04).
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